Mine is a toss up between walking passed a ticketmaster outlet and finding out that the Stones were doing a second concert at Shea Stadium and ran and got on line, and got amazing seats, for like $50....
OR the Guns and Roses concert, where Metallica opened for them and BLEW AWAY GNR....

John Williams and the New York Philharmonic at Lincoln Center was a big deal for me.

Rock concerts:

Genesis at Veterans Stadium early 90s

Emerson Lake and Palmer at Mann Music Center early 90s

Allman Brothers @ Spectrum early 90s

Dio at Spectrum 1986

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I saw the Allmans at the Spectrum in 89-90, i cannot remember the exact year - Drove down on a whim and got there a little late. Box office was closed and couldnt get tickets. We bumped into a guy had 2 tix for someone that didnt show. 3rd floor floor seats! We missed the whole first set but that 2nd set alone is in my top 3 concerts ever. They BLEW me away.

Saw Waters do the Wall at the United Center (Bulls) in2010. Great show.

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The theatrics were awesome in 1990. There were a lot of hiccups with the sound and other shit. The list of guests were good but some songs sounded pretty shitty during the concert but it was fixed on the CD/DVD. But it was like 7 months after the Berlin Wall came down so there was a feeling in the air that i cannot explain.